This article examines the experiences of 25 persons who were assigned female status at birth but do not wish to live as women and take on a masculine or queer gender identity. We employ the concept of “gendered embodiment” and introduce the concept of “sexualized embodiment” to highlight what is involved in this process. We ask how experiencing a masculine gender identity is reflexively tied to a trans man's sexuality and the ways in which these two embodiments are tightly, moderately, or loosely coupled. For example, a tight coupling appeared when trans men began to use testosterone and obtained surgery such as breast removal; a moderate coupling was found where gender validation was sought from a sexual partner (with this being related to sexual preference identities as well as the interpretation of vaginal penetration); the loosest coupling of the gender‐sexuality embodiments was linked to the liberality of the locale and whether “queer” identities could be easily adopted. In sum, our research demonstrates the link between gender and sexuality as a result of the body work trans men do and the historical and geographical situations in which they find themselves.